4-Hydroxy-6-(2,4,5-trimethoxy-phenyl)-pyran-2-one | 256408-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Hydroxy-6-(2,4,5-trimethoxy-phenyl)-pyran-2-one
• 英文别名: 4-Hydroxy-6-(2,4,5-trimethoxyphenyl)pyran-2-one；4-hydroxy-6-(2,4,5-trimethoxyphenyl)pyran-2-one
• CAS: 256408-81-8
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: OCLVZAANJFPVLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-甲基-2-丁烯醛 、 4-Hydroxy-6-(2,4,5-trimethoxy-phenyl)-pyran-2-one 在 哌啶 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 以78%的产率得到2,2-Dimethyl-7-(2,4,5-trimethoxy-phenyl)-2H-pyrano[4,3-b]pyran-5-one
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes

  摘要：

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.

  DOI：

  10.1021/jo020688t
• 作为产物：
  描述：

  2,4,5-三甲氧苯甲酸甲酯 在 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， -78.0~150.0 ℃ 、399.97 Pa 条件下， 生成 4-Hydroxy-6-(2,4,5-trimethoxy-phenyl)-pyran-2-one
  参考文献：
  名称：

  Synthesis and UV Studies of A Small Library of 6-Aryl-4-hydroxy-2-pyrones. A Relevant Structural Feature for the Inhibitory Property of Arisugacin Against Acetylcholinesterase

  摘要：

  4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that ale biologically relevant. We describe here preparations of a small library of 6-aryl-4-hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy-pyrones are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00847-9

文献信息

• A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
  作者：Hong C. Shen、Jiashi Wang、Kevin P. Cole、Michael J. McLaughlin、Christopher D. Morgan、Christopher J. Douglas、Richard P. Hsung、Heather A. Coverdale、Aleksey I. Gerasyuto、Juliet M. Hahn、Jia Liu、Heather M. Sklenicka、Lin-Li Wei、Luke R. Zehnder、Craig A. Zificsak

  DOI：10.1021/jo020688t

  日期：2003.3.1

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.
• Synthesis and UV Studies of A Small Library of 6-Aryl-4-hydroxy-2-pyrones. A Relevant Structural Feature for the Inhibitory Property of Arisugacin Against Acetylcholinesterase
  作者：Christopher J. Douglas、Heather M. Sklenicka、Hong C. Shen、David S. Mathias、Shane J. Degen、Geoffrey M. Golding、Christopher D. Morgan、Regina A. Shih、Kristen L. Mueller、Lisa M. Scurer、Erik W. Johnson、Richard P. Hsung

  DOI：10.1016/s0040-4020(99)00847-9

  日期：1999.11

  4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that ale biologically relevant. We describe here preparations of a small library of 6-aryl-4-hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy-pyrones are described. (C) 1999 Elsevier Science Ltd. All rights reserved.